US6797731B2ExpiredUtilityPatentIndex 46

Resorcinol derivatives

Assignee: PFIZERPriority: Sep 21, 2000Filed: Mar 12, 2003Granted: Sep 28, 2004

Est. expirySep 21, 2020(expired)· nominal 20-yr term from priority

Inventors:BRADLEY STUART E COLLINGTON ERIC W FYFE MATTHEW C GATTRELL WILLIAM T GEDEN JOANNA V MURRAY PETER J PROCTER MARTIN J ROWLEY ROBERT J WILLIAMS JONATHAN G

A61P 29/00C07C 2601/14C07C 311/49C07D 317/72A61Q 19/02A61K 8/42C07D 235/24C07C 255/36C07C 235/36C07C 233/58A61K 8/70A61P 17/06C07D 231/16C07C 271/56A61P 17/00C07D 307/24C07D 231/14C07C 59/54A61K 8/4926A61K 8/69A61K 8/492A61K 8/35C07C 2601/16C07D 207/16C07D 207/267C07C 275/28A61P 17/02A61K 8/4973C07C 69/96C07D 487/04C07D 307/94A61K 8/4946C07D 339/06C07D 209/42A61K 8/4986C07D 333/38C07C 271/66C07C 233/23C07C 255/57C07D 213/81C07D 213/82C07D 209/24C07D 307/79C07C 271/24C07C 69/732C07C 233/74C07D 303/14C07D 237/04C07D 213/56C07C 259/10

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Claims

Abstract

The present invention relates to certain resorcinol derivatives and their use as skin lightening agents.

Claims

exact text as granted — not AI-modified

What is claimed is:  
     
       1. A cosmetic composition comprising a cosmetically acceptable topical carrier in combination with an effective amount of a compound of formula I                    
       or a pharmaceutically acceptable salt thereof, wherein: 
       R is a (C 3 -C 8 )cycloalkyl or (C 5 -C 8 )cycloalkenyl ring substituted by —N(R 1 )CONR 2 R 3  wherein R 1  and R 2  are independently selected from hydrogen, (C 1 -C 6 )alkyl, and aryl(C 1 -C 6 )alkyl, and R 3  is hydrogen, (C 1 -C 6 )alkyl-, aryl(C 1 -C 6 )alkyl, or aryl; —N(R 4 )COR 5  wherein R 4  is hydrogen, (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl-, or OH and R 5  is (C 7 -C 10 )alkyl, aryl, aryl(C 1 -C 6 )alkyl-, —Oaryl, CF 3 , heterocycloalkyl, —(C 1 -C 6 )alkylheterocycloalkyl, —(C 2 -C 7 )alkenylheterocycloalkyl, heteroaryl, —(C 1 -C 6 )alkylheteroaryl, —(C 2 -C 7 )alkenylheteroaryl, —(C 2 -C 7 )alkenlaryl, —(C 2 -C 7 )alkenylCOaryl, —(C 1 -C 6 )alkylN(R 4 )CO-aryl, —(C 1 -C 6 )alkylCO-aryl, —(C 1 -C 6 )alkylhydroxyaryl, —(C 1 -C 6 )alkyl-X-aryl, (C 2 -C 7 )alkenyl, benzyhydryl, 5-hydroxyoxoindanyl, or tetrahydronaphthanenyl, wherein X is O, S, SO, SO 2  or NR 1 ; —N(R 1 ) OCOaryl; ═CHCO 2 R 1 ; ═CHCONR 1 R 2 ; ═CHCN; ═NNHSO 2 R 6  wherein R 6  is aryl; —N(O)═CHR 6 ; —OC(O)NR 1 R 7  wherein R 7  is aryl, aryl(C 1 -C 6 )alkyl-, —(C 1 -C 6 )alkylCO 2 (C 1 -C 6 )alkyl, —CO 2 (C 1 -C 6 )alkyl, —CO 2 aryl, or —CO 2 (C 1 -C 6 )alkylaryl; amino(C 1 -C 6 )alkylarylCO 2 —; or —OC(O)OR 8  wherein R 8  is (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl, or aryl;  
       with the proviso that the cycloalkenyl ring is not aromatic.  
     
     
       2. A method for inhibiting tyrosinase in a human comprising administering to said human an effective amount of compound of formula I.                    
       or a pharmaceutically acceptable salt thereof, wherein: 
       R is a (C 3 -C 8 )cycloalkyl or (C 5 -C 8 )cycloalkenyl ring substituted by —N(R 1 )CONR 2 R 3  wherein R 1  and R 2  are independently selected from hydrogen, (C 1 -C 6 )alkyl, and aryl(C 1 -C 6 )alkyl, and R 3  is hydrogen, (C 1 -C 6 )alkyl-, aryl(C 1 -C 6 )alkyl, or aryl; —N(R 4 )COR 5  wherein R 4  is hydrogen, (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl-, or OH and R 5  is (C 7 -C 10 )alkyl, aryl, aryl(C 1 -C 6 )alkyl-, —Oaryl, CF 3 , heterocycloalkyl, —(C 1 -C 6 )alkylheterocycloalkyl, —(C 2 -C 7 )alkenylheterocycloalkyl, heteroaryl, —(C 1 -C 6 )alkylheteroaryl, —(C 2 -C 7 )alkenylheteroaryl, —(C 2 -C 7 )alkenlaryl, —(C 2 -C 7 )alkenylCOaryl, —(C 1 -C 6 )alkylN(R 4 )CO-aryl, —(C 1 -C 6 )alkylCO-aryl, —(C 1 -C 6 )alkylhydroxyaryl, —(C 1 -C 6 )alkyl-X-aryl, (C 2 -C 7 )alkenyl, benzyhydryl, 5-hydroxyoxoindanyl, or tetrahydronaphthanenyl, wherein X is O, S, SO, SO 2  or NR 1 ; —N(R 1 ) OCOaryl; ═CHCO 2 R 1 ; ═CHCONR 1 R 2 ; ═CHCN; ═NNHSO 2 R 6  wherein R 6  is aryl; —N(O)═CHR 6 ; —OC(O)NR 1 R 7  wherein R 7  is aryl, aryl(C 1 -C 6 )alkyl-, —(C 1 -C 6 )alkylCO 2 (C 1 - 6 )alkyl, —C 2 (C 1 -C 6 )alkyl, —COO 2 aryl, or —CO 2 (C 1 -C 6 )alkylaryl; amino(C 1 -C 6 )alkylarylCO 2 —; or —OC(O)OR 8  wherein R 8  is (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl, or aryl;  
       with the proviso that the cycloalkenyl ring is not aromatic.  
     
     
       3. A method for treating a human afflicted with an inflammatory disorder selected from the group consisting of psoriasis, dermatitis, acne and dandruff comprising topically administering to said human a compound of formula I                    
       or a pharmaceutically acceptable salt thereof, wherein: 
       R is a (C 3 -C 8 )cycloalkyl or (C 5 -C 8 )cycloalkenyl ring substituted by —N(R 1 )CONR 2 R 3  wherein R 1  and R 2  are independently selected from hydrogen, (C 1 -C 6 )alkyl, and aryl(C 1 -C 6 )alkyl, and R 3  is hydrogen, (C 1 -C 6 )alkyl-, aryl(C 1 -C 6 )alkyl, or aryl; —N(R 4 )COR 5  wherein R 4  is hydrogen, (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl-, or OH and R 5  is (C 7 -C 10 )alkyl, aryl, aryl(C 1 -C 6 )alkyl-, —Oaryl, CF 3 , heterocycloalkyl, —(C 1 -C 6 )alkylheterocycloalkyl, —(C 2 -C 7 )alkenylheterocycloalkyl, heteroaryl, —(C 1 -C 6 )alkylheteroaryl, —(C 2 -C 7 )alkenylheteroaryl, —(C 2 -C 7 )alkenlaryl, —(C 2 -C 7 )alkenylCOaryl, —(C 1 -C 6 )alkylN(R 4 )CO-aryl, —(C 1 -C 6 )alkylCO-aryl, —(C 1 -C 6 )alkylhydroxyaryl, —(C 1 -C 6 )alkyl-X-aryl, (C 2 -C 7 )alkenyl, benzyhydryl, 5-hydroxyoxoindanyl, or tetrahydronaphthanenyl, wherein X is O, S, SO, SO 2  or NR 1 ; —N(R 1 ) OCOaryl; ═CHCO 2 R 1 ; CHCONR 1 R 2 ; ═CHCN; ═NNHSO 2 R 6  wherein R 6  is aryl; —N(O)═CHR 6 ; —OC(O)NR 1 R 7  wherein R 7  is aryl, aryl(C 1 -C 6 )alkyl-, —(C 1 -C 6 )alkylCO 2 (C 1 -C 6 )alkyl, —CO 2 (C 1 -C 6 )alkyl, —CO 2 aryl, or —CO 2 (C 1 -C 6 )alkylaryl; amino(C 1 -C 6 )alkylarylCO 2 —; or —OC(O)R 8  wherein R 8  is (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl, or aryl;  
       with the proviso that the cycloalkenyl ring is not aromatic.  
     
     
       4. A method for the treatment of disorders of human pigmentation comprising topically administering to said human an effective amount of a compound of formula I.                    
       or a pharmaceutically acceptable salt thereof, wherein: 
       R is a (C 3 -C 8 )cycloalkyl or (C 5 -C 8 )cycloalkenyl ring substituted by —N(R 1 )CONR 2 R 3  wherein R 1  and R 2  are independently selected from hydrogen, (C 1 -C 6 )alkyl, and aryl(C 1 -C 6 )alkyl, and R 3  is hydrogen, (C 1 -C 6 )alkyl-, aryl(C 1 -C 6 )alkyl, or aryl; —N(R 4 )COR 5  wherein R 4  is hydrogen, (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl-, or OH and R 5  is (C 7 -C 10 )alkyl, aryl, aryl(C 1 -C 6 )alkyl-, —Oaryl, CF 3 , heterocycloalkyl, —(C 1 -C 6 )alkylheterocycloalkyl, —(C 2 -C 7 )alkenylheterocycloalkyl, heteroaryl, —(C 1 -C 6 )alkylheteroaryl, —(C 2 -C 7 )alkenylheteroaryl, —(C 2 -C 7 )alkenlaryl, —(C 2 -C 7 )alkenylCOaryl, —(C 1 -C 6 )alkylN(R 4 )CO-aryl, —(C 1 -C 6 )alkylCO-aryl, —(C 1 -C 6 )alkylhydroxyaryl, —(C 1 -C 6 )alkyl-X-aryl, (C 2 -C 7 )alkenyl, benzyhydryl, 5-hydroxyoxoindanyl, or tetrahydronaphthanenyl, wherein X is O, S, SO, SO 2  or NR 1 ; —N(R 1 ) OCOaryl; ═CHCO 2 R 1 ; ═CHCONR 1 R 2 ; ═CHCN; ═NNHSO 2 R 6  wherein R 6  is aryl; —N(O)═CHR 6 ; —OC(O)NR 1 R 7  wherein R 7  is aryl, aryl(C 1 -C 6 )alkyl-, —(C 1 -C 6 )alkylCO 2 (C 1 -C 6 )alkyl, —CO 2 (C 1 -C 6 )alkyl, —CO 2 aryl, or —CO 2 (C 1 -C 6 )alkylaryl; amino(C 1 -C 6 )alkylarylCO 2 —; or —OC(O)OR 8  wherein R 8  is (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl, or aryl;  
       with the proviso that the cycloalkenyl ring is not aromatic.  
     
     
       5. A method according to  claim 4  in which said disorder is selected from the group consisting of solar lentigines and simple lentigines. 
     
     
       6. A method for cosmetically lightening skin comprising topically administering to a human in need of such an effect a cosmetically effective amount of a compound according to formula I                    
       or a pharmaceutically acceptable salt thereof, wherein: 
       R is a (C 3 -C 8 )cycloalkyl or (C 5 -C 8 )cycloalkenyl ring substituted by —N(R 1 )CONR 2 R 3  wherein R 1  and R 2  are independently selected from hydrogen, (C 1 -C 6 )alkyl, and aryl(C 1 -C 6 )alkyl, and R 3  is hydrogen, (C 1 -C 6 )alkyl-, aryl(C 1 -C 6 )alkyl, or aryl; —N(R 4 )COR 5  wherein R 4  is hydrogen, (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl-, or OH and R 5  is (C 7 -C 10 )alkyl, aryl, aryl(C 1 -C 6 )alkyl-, —Oaryl, CF 3 , heterocycloalkyl, —(C 1 -C 6 )alkylheterocycloalkyl, —(C 2 -C 7 )alkenylheterocycloalkyl, heteroaryl, —(C 1 -C 6 )alkylheteroaryl, —(C 2 -C 7 )alkenylheteroaryl, —(C 2 -C 7 )alkenlaryl, —(C 2 -C 7 )alkenylCOaryl, —(C 1 -C 6 )alkylN(R 4 )CO-aryl, —(C 1 -C 6 )alkylCO-aryl, —(C 1 -C 6 )alkylhydroxyaryl, —(C 1 -C 6 )alkyl-X-aryl, (C 2 -C 7 )alkenyl, benzyhydryl, 5-hydroxyoxoindanyl, or tetrahydronaphthanenyl, wherein X is O, S, SO, SO 2  or NR 1 ; —N(R 1 ) OCOaryl; ═CHCO 2 R 1 ; ═CHCONR 1 R 2 ; ═CHCN; ═NNHSO 2 R 6  wherein R 6  is aryl; —N(O)═CHR 6 ; —OC(O)NR 1 R 7  wherein R 7  is aryl, aryl(C 1 -C 6 )alkyl-, —(C 1 -C 6 )alkylCO 2 (C 1 -C 6 )alkyl, —CO 2 (C 1 -C 6 )alkyl, -CO 2 aryl, or —C 2 (C 1 -C 6 )alkylaryl; amino(C 1 -C 6 )alkylarylCO 2 —; or —OC(O)OR 8  wherein R 8  is (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl, or aryl;  
       with the proviso that the cycloalkenyl ring is not aromatic.

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